Showing metabocard for 2-Oxo-4-methylthiobutanoic acid (MMDBc0000573)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:40:51 UTC
Update Date2022-08-31 06:10:00 UTC
Metabolite IDMMDBc0000573
Metabolite Identification
Common Name2-Oxo-4-methylthiobutanoic acid
Description2-oxo-4-methylthiobutanoate, also known as 2-keto-4-methylthiobutyric acid, 2-keto-4-methylthiobutyrate or 4-(methylsulfanyl)-2-oxobutanoic acid, is a member of the class of compounds known as thia- fatty acids. Thia-fatty acids are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain. Thus, 2-oxo-4-methylthiobutanoate is a fatty acid lipid molecule. 2-oxo-4-methylthiobutanoate is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 2-oxo-4-methylthiobutanoate can be synthesized from L-methionine and butyric acid. 2-oxo-4-methylthiobutanoate can also be synthesized into S-adenosyl-4-methylthio-2-oxobutanoic acid. 2-oxo-4-methylthiobutanoate can be found in a number of food items such as cloves, highbush blueberries, common beets, and cashew nuts. 2-oxo-4-methylthiobutanoate can be found in urine. Within the cell, 2-oxo-4-methylthiobutanoate is primarily located in the cytoplasm and in the membrane. 2-oxo-4-methylthiobutanoate has been found in all living species, from bacteria to humans. In humans, 2-oxo-4-methylthiobutanoate is found to be involved in several metabolic disorders, some of those are S-adenosylhomocysteine (SAH) hydrolase deficiency, methylenetetrahydrofolate reductase deficiency (MTHFRD), methionine adenosyltransferase deficiency, and glycine N-methyltransferase deficiency. 4-Methylthio-2-oxobutanoic acid is the direct precursor of methional, which is a potent inducer of apoptosis in a BAF3 murine lymphoid cell line which is interleukin-3 (IL3)-dependent (PMID: 7848263 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f5abf7ae6f0>


  Mrv1652309042000242D          

  9  8  0  0  0  0            999 V2000
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f5abf7ae6f0>

HMDB0001553
     RDKit          3D
2-Oxo-4-methylthiobutanoic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
    3.6581   -0.1397    0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2216   -0.3887   -0.7817 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7466    0.0188    0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5177   -0.1559   -0.6188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7098    0.1814    0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5942    0.5549    1.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0544    0.0947   -0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1890   -0.2761   -1.5501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1907    0.3976    0.3568 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5725    0.0852   -0.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8484   -1.0539    0.9210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4166    0.6783    1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195    1.1049    0.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6926   -0.6022    1.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5664   -1.2024   -0.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4884    0.5024   -1.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6655    1.2734    0.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  9 17  1  0
M  END
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3D SDF for #<Metabolite:0x00007f5abf7ae6f0>


  Mrv1652309042000242D          

  9  8  0  0  0  0            999 V2000
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000573

> <DATABASE_NAME>
MIME

> <SMILES>
CSCCC(=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O3S/c1-9-3-2-4(6)5(7)8/h2-3H2,1H3,(H,7,8)

> <INCHI_KEY>
SXFSQZDSUWACKX-UHFFFAOYSA-N

> <FORMULA>
C5H8O3S

> <MOLECULAR_WEIGHT>
148.18

> <EXACT_MASS>
148.019414812

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
14.212411248449321

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(methylsulfanyl)-2-oxobutanoic acid

> <ALOGPS_LOGP>
-0.07

> <JCHEM_LOGP>
1.1240172496666667

> <ALOGPS_LOGS>
-1.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.823095177292476

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.303792429217063

> <JCHEM_PKA_STRONGEST_BASIC>
-9.673901775734686

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
35.0709

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-oxo-4-thiomethylbutyric acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f5abf7ae6f0>

HMDB0001553
     RDKit          3D
2-Oxo-4-methylthiobutanoic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
    3.6581   -0.1397    0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2216   -0.3887   -0.7817 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7466    0.0188    0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5177   -0.1559   -0.6188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7098    0.1814    0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5942    0.5549    1.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0544    0.0947   -0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1890   -0.2761   -1.5501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1907    0.3976    0.3568 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5725    0.0852   -0.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8484   -1.0539    0.9210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4166    0.6783    1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195    1.1049    0.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6926   -0.6022    1.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5664   -1.2024   -0.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4884    0.5024   -1.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6655    1.2734    0.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  9 17  1  0
M  END
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PDB for #<Metabolite:0x00007f5abf7ae6f0>

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       4.620   2.667   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.621   4.977   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for #<Metabolite:0x00007f5abf7ae6f0>

COMPND    HMDB0001553
HETATM    1  C1  UNL     1       3.658  -0.140   0.299  1.00  0.00           C  
HETATM    2  S1  UNL     1       2.222  -0.389  -0.782  1.00  0.00           S  
HETATM    3  C2  UNL     1       0.747   0.019   0.192  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.518  -0.156  -0.619  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.710   0.181   0.193  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.594   0.555   1.389  1.00  0.00           O  
HETATM    7  C5  UNL     1      -3.054   0.095  -0.358  1.00  0.00           C  
HETATM    8  O2  UNL     1      -3.189  -0.276  -1.550  1.00  0.00           O  
HETATM    9  O3  UNL     1      -4.191   0.398   0.357  1.00  0.00           O  
HETATM   10  H1  UNL     1       4.572   0.085  -0.307  1.00  0.00           H  
HETATM   11  H2  UNL     1       3.848  -1.054   0.921  1.00  0.00           H  
HETATM   12  H3  UNL     1       3.417   0.678   1.002  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.820   1.105   0.427  1.00  0.00           H  
HETATM   14  H5  UNL     1       0.693  -0.602   1.104  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.566  -1.202  -0.981  1.00  0.00           H  
HETATM   16  H7  UNL     1      -0.488   0.502  -1.502  1.00  0.00           H  
HETATM   17  H8  UNL     1      -4.666   1.273   0.215  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3
CONECT    3    4   13   14
CONECT    4    5   15   16
CONECT    5    6    6    7
CONECT    7    8    8    9
CONECT    9   17
END
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SMILES for #<Metabolite:0x00007f5abf7ae6f0>

CSCCC(=O)C(O)=O
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INCHI for #<Metabolite:0x00007f5abf7ae6f0>

InChI=1S/C5H8O3S/c1-9-3-2-4(6)5(7)8/h2-3H2,1H3,(H,7,8)
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Synonyms
ValueSource
2-Keto-4-methylthiobutyric acidChEBI
2-oxo-4-MethylthiobutanoateChEBI
2-OxomethionineChEBI
4-(METHYLsulfanyl)-2-oxobutanoIC ACIDChEBI
4-Methylthio-2-oxobutanoateChEBI
alpha-oxo-gamma-Methylthiobutyric acidChEBI
4-(Methylsulfanyl)-2-oxobutanoateKegg
2-Keto-4-methylthiobutyrateGenerator
4-(METHYLsulphanyl)-2-oxobutanoateGenerator
4-(METHYLsulphanyl)-2-oxobutanoic acidGenerator
4-Methylthio-2-oxobutanoic acidGenerator
a-oxo-g-MethylthiobutyrateGenerator
a-oxo-g-Methylthiobutyric acidGenerator
alpha-oxo-gamma-MethylthiobutyrateGenerator
Α-oxo-γ-methylthiobutyrateGenerator
Α-oxo-γ-methylthiobutyric acidGenerator
2-KetomethiobutyrateHMDB
4-Methylthio-2-ketobutanoateHMDB
4-Methylthio-2-ketobutanoic acidHMDB
4-Methylthio-2-ketobutyrateHMDB
4-Methylthio-2-oxobutyrateHMDB
alpha-Keto-methiolbutyric acidHMDB
Keto-4-methylthiobutyrateHMDB
KetomethiobutyrateHMDB
Ketomethiobutyric acidHMDB
KMTBHMDB
MethylthiobutyrateHMDB
Methylthiobutyric acidHMDB
2-Keto-4-methylthiobutanoic acidHMDB
2-Keto-4-thiomethylbutyrateHMDB
2-oxo-4-Thiomethylbutyric acidHMDB
alpha-Keto-gamma-methiolbutyrateHMDB
alpha-KetomethionineHMDB
alpha-OxomethionineHMDB
2-Keto-4-methylthiobutyric acid, monosodium saltHMDB
2-Ketothiomethylbutyric acidHMDB
4-Methylthio-2-oxobutyric acidHMDB
S-Methyl-alpha-ketobutyric acidHMDB
2-Keto-4-methylthiobutyric acid, calcium saltHMDB
4-Methylthio-2-ketobutyric acidHMDB
gamma-Methiol-keto-butyric acidHMDB
4-Methylmercapto-2-oxobutyrateHMDB
2-oxo-4-Methylthiobutanoic acidKEGG
Molecular FormulaC5H8O3S
Average Mass148.18
Monoisotopic Mass148.019414812
IUPAC Name4-(methylsulfanyl)-2-oxobutanoic acid
Traditional Name2-oxo-4-thiomethylbutyric acid
CAS Registry NumberNot Available
SMILES
CSCCC(=O)C(O)=O
InChI Identifier
InChI=1S/C5H8O3S/c1-9-3-2-4(6)5(7)8/h2-3H2,1H3,(H,7,8)
InChI KeySXFSQZDSUWACKX-UHFFFAOYSA-N